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So-and-So Just Died
 and You’re Still Checking Boxes?

May 20, 2025
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Let’s go there.

If you’re anything like me, you’ve probably been getting more and more of those messages lately—the “Did you hear?” texts. The “Gone too soon” Facebook posts.

53. 58. 64.
And it hits you.
What the actual f**k?

Worked their whole life.
Busted their ass.
Sacrificed vacations, skipped the fun, stressed over deadlines and health benefits...
And just like that—they’re gone.

No retirement.
No grand adventure.
No sipping wine on a Tuscan balcony with the person they love.
Just a damn GoFundMe and some well-meaning clichés in the comments.

Let me be real with you: This? This is your wake-up call.

 

We’ve Been Sold a Lie

I don’t know when we decided that “success” meant living life in pursuit of “someday.”

Someday we’ll travel.
Someday we’ll slow down.
Someday we’ll finally feel happy once the debt’s paid, the house is remodeled, the kids are grown, the dog stops puking on the rug


But someday is not a plan.
It’s a trap.

And if you’re not careful, you’ll spend your one and only life:

  • Working for a retirement you might never get to enjoy.

  • Prioritizing a “legacy” for people who just want you to be present.

  • Dying with a full bank account and an empty life.

Where the hell did we take this hard left into living like that’s normal?

 

I’m Not Knocking Stability—But Let’s Be Honest

Look—I get it. I used to be the guy chasing the promotions, the bonuses, the quarterly reviews. 

I had the title, the income, the nice vacation photos (and the massive stress hangovers to go with them).

And then I woke up one day and realized:
I was spending my life earning a lifestyle I didn’t even have time to enjoy.

Let that sink in.

I was so busy building the “dream” that I forgot to actually live it.

And then came the messages:

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Midlife Chronicles

Midlife Recreated: At 52, I ditched the “shoulds” and rewrote the script. Now it’s your turn. Let me help you build a life of joy, travel, purpose—and fewer boring expectations. 50 Shades of Should isn’t a crisis—it’s a comeback to Your Dreams!
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